


Truth or Dare Fun

by R2girl07



Category: Supernatural RPF
Genre: Drinking, F/M, Fluff and Smut, Kissing, Truth or Dare
Language: English
Status: Completed
Published: 2021-02-27
Updated: 2021-02-27
Packaged: 2021-03-18 06:02:25
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,411
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29729439
Author URL: https://archiveofourown.org/users/R2girl07/pseuds/R2girl07
Summary: *Rob Benedict x reader*While at a convention, some of the cast play a game of truths in between the panels. The questions get juicier and juicier until someone) brings up first time having sex. But the reader is a virgin and she lies about it. Rob notices her getting uncomfortable and decides to confront her about it later. Lots of fluff, but some smut too.I want to add I'm making it to where Rob is still married but is separated from his wife and is about to go through with his divorce but none of the other cast members know but he tells the reader after drinking.
Relationships: Rob Benedict/Reader, Rob Benedict/You
Kudos: 3





	Truth or Dare Fun

You've been part of the SPN conventions for a few years now. You're friends with all the cast. They are all amazing and you love them all like family. Except Rob Benedict from the moment you met him on set you fell for him hard. You'd never let him in on that.

Over the years Rich, Kim, Briana and Ruth have teased the two of you about how the two of you are always flirting. You always blush and deny it. You usually don't take part in the games and drinking that take place with all the other cast but Rich had been aggravating you all day to come and play truth or dare with them in between panels.

"Come on sugar it will be fun and Rob will be there!" He wiggles his eyebrows at the last part giving you a smirk. "Richard what does Rob have to do with me playing truth or dare?" He smirks "It has everything to do with it Y/N!" You sigh knowing that if you don't say yes he will keep nagging. "Okay fine! I'll come play!"

You glance across the room noticing Rob strumming on his guitar with Billy. You watch him for a moment blushing as he looks up at you. He gives you a smirk and you blush harder and quickly look away. You sit on the couch next to Mark Pellegrino and nervously pull out your phone. You pull up twitter and start scrolling not really paying attention. You jump hearing Mark's voice in your ear. "Y/N you okay you seem really nervous?" You look up at him giving a fake smile. "Yeah Pellegrino I'm fine." You nervously glace over to Rob to see he's already watching you. You quickly look away blushing again. "I think I know why your so nervous." He chuckles as your handler comes in and says its time for your panel with Rob and Rich.

You get up as Rob gets up with the rest of the band and start following them with your handler. You smile watching Rob's ass in those tight jeans he always wears. You jump hearing Richard's teasing voice. "You enjoying the view Y/N?" You blush and slap him. He chuckles as you all reach backstage. Billy, Stephen, and Mike go out first and start playing. Rich starts talking into a microphone as he runs out. "Hey everybody! Give it up for Rob!" Rob runs out "Richard Speight everybody!" The crowd gets louder. You take a deep breath as Rob starts talking again. "Okay guys lets hear it for the beautiful talented Y/N!"

You run out smiling. Rob pulls you to him hugging you tightly. You blush hoping the crowd doesn't notice. Richard notices and immediately points it out. "Y/N are you hot? Your cheeks look a little flushed!" The crowd giggles and Rob chuckles softly. "Richard leave her alone! She's probably nervous!" He touches the small of your back sending chills everywhere. "Okay you two! Enough about me. Let's get this show on the road." You point one side of the room to a fan waiting to ask a question. The whole panel you hold your breath as Rob every so often touches your arm or glances at you.

An hour later everyone has about an hour down time. "So Y/N Rich says your coming to play Truth or Dare with us!" You nervously look over at Briana and nod. She smiles grabbing your arm walking with you to the elevators to go to her room where everyone meets. The two of you make it to her room seeing Jared, Jensen, Mark Pellegrino, Misha, Kim, Ruth, Felica, Rich, Billy Moran, Stephen Norton, Mike Borja and Rob are already there.

As soon as you walk in you can't help but notice Rob sitting on the bed with Rich and Billy. He's wearing his glasses and you can't help but let out a sigh. Bri pushes you forward as she closes the door. Kim walks up to you offering you a beer which you decline. She smiles at you "I'm glad you decided to come join us today Y/N." You nod nervously. She pulls you next to her on the couch next to the bed. Rob looks at you giving a smirk causing chills to go everywhere again.

You quickly look away. You hear Felica say "Let's get the fun started! I'll go first. Misha Truth or Dare?" Misha smirks "Truth!" Felica is quite for a moment thinking of a good question. "What's one movie you're embarrassed to admit you enjoy?" Misha thinks for moment "White Chicks. Mark Truth or Dare?"

"Dare!"

"I dare you to text your wife and say your horny and want to some sexy pictures."

Mark smirks as he pulls out his phone and texts his wife showing everyone it sent.

You watch as they all go back and forth. After a while of everyone drinking the questions start to get a little personal. Kim asks Bri "Truth or Dare Bri!"

Bri giggles "Truth!"

"What's your biggest turn-on?" Bri laughs thinking as she reveals her biggest turn on. "Rob Truth or Dare?" Rob looks over at you for a moment "Dare!"

"I dare you to kiss Misha on the lips!" Rob chuckles but gets up kissing Misha without hesitation. "Rich truth or Dare?" Rich looks at Rob "Dare!" Rob gets a big smirk "I dare you to text Jaci and your the man of the house and you aren't taking anymore shit from her." Rich looks at Rob as if questioning if he is serious. I chuckle as he shakily pulls out his phone and pulls up Jaci. He types the message but pauses staring at it. You chuckle. "You gonna send it or not Rich!" He looks up at you fear in his eyes but you hear it send.

Rob looks at him. "Shit man! Did you really send her that!!!" Richard nods. "Holy hell dude you're fucked!" Rich swallows. "Kim truth or Dare?" "Truth!" Richard asks her "How many people have you kissed?" Kim gives her anwser. "Okay Y/N your turn truth or dare?" You swallow "Truth?"

She thinks for a moment. "When was the first time you had sex and what was it like?"

You panic for a moment thinking to yourself What do I do I've never had sex before. Do I lie? You fidget for a moment and you stutter out. "I-uh was...18..It was at...a...uh..party. It...was umm...okay..I guess." You look down blushing. You can feel them all staring at you. Looking down you just ask. "umm Billy Truth or dare." Billy quietly says "Truth"

"Umm..Did you teach yourself to play guitar?" He chuckles "Yeah!" They go back and forth for a while asking each other more sexual things. You start to feel uneasy and out of place. "Umm guys I'm feeling kinda tired. I think i'm going to back to my room and get some rest." Before any of the can protest your already to the door and out.

You rush down the hall to your room you fumble with your keycard and finally get it open. Once you're inside you let out a breath. As you walk away from the door you hear a soft knock on your door. Who the hell could that be? You walk to the door and look through the peephole. Seeing its Rob you get nervous all over again. You debate on whether of not to answer. Maybe if I'm really quite and still he will go away.

He knocks again. "Y/N it's Rob?" You take a deep breath and open the door. "Can I help you Robbie?" He smiles "I just wanted to make sure you were okay. You seemed kinda nervous after Kim asked you that question." You blush "Yeah i'm okay but I'm tired so I'll talk to you later." You go to close the door but he puts his hand out stopping it. "I have a feeling your not being honest with me." You swallow as he pushes his way into your room.

He moves toward you watching you through his glasses. You stumble backwards trying to get away from him. He smirks stopping. "Can I ask you something Y/N." You look at him for a moment and nod. "Have you ever had sex?" You stare at him blushing. "I-uh...! Yes!" He grins moving closer to you. He grabs your face in his hands his face inches from yours. "So you'd be okay if I did this..." He leans in right as his lips are about to touch yours you pull away. "Okay Robbie I'm a virgin! I've never had sex! You happy there I said it! You going to make fun of me like everyone else does." He stands there for a moment as if trying to read my face. "Y/N sweetheart why would I make fun of you. Being a virgin isn't a bad thing."

Did he just call me sweetheart!

"That's easy for you to say! You're married and you have two kids!"

Rob smiles moving toward you again this time he grabs your hips and pulls you to him. Before you have time to react his lips are crashing into yours. At first you don't know what to do but after a moment you relax and his him back. He pulls away causing your cheeks to flush again.

One of his hands finds your cheek. "I can help you not be a virgin if you want."

"Robbie what the hell are you talking about?"

He smirks as one of his hands wonders to your ass as he leans in kissing your neck lightly he whispers sending chills down your spine. "What do you think I mean sweetheart? I've been eyeing you all day in these damn shorts of yours. Wondering what you look like out of them."

"Rob? Aren't you married?" He groans as his hands wonder your body causing a fire within. You've wanted this moment for so long. "I've got a secret Y/N! Molly and I have been separated from months now and we are filling for divorce. I haven't had sex in so long and I've always been attracted to you. You're so damn beautiful!"

Your hands roam to his hair and pull lightly as he continues to kiss your neck. Your body is on fire as his hands find the button your shorts you come to your senses thinking he's drunk. You quickly push him off causing him to look at you confused. "Robbie your drunk. You need to go take a cold shower and sober up and maybe we'll talk later." He sighs as he starts pulling off his shirt. "UMM Rob! I didn't mean here! I meant go back to your own room!!" He turns walking toward the door but ends up passing out on the couch instead.

You sigh grabbing a blanket from the bed and throwing it over him. You decide to let him snooze hoping he'll be sobered enough by the time Karaoke comes around. Thirty minutes pass and you see him stirring on the couch. He rolls over grabbing his head. "Morning sunshine!"

His head whips toward you. "Where the hell am I and why is my head hurting." You chuckle. "You're in my room. You followed me here after I left Kim's room and you've got a hangover." You throw him a bottle of Ibuprofen he catches it groaning. He opens the bottle taking out two and putting it in front of him. He grabs his hand as he goes to get up "Fuck!" He notices his shirt is unbuttoned and looks over at you. "Did we?" You chuckle nervously "Umm...No we didn't do anything but you kinda did come on to me and you might have mentioned about you and Molly getting a divorce soon."

"Shit Y/N I'm so sorry! I get weird when I'm drunk!" You start to get nervous again. "Rrrooobbb do you rrreeemmmmeber anything I said?"

He gives me a questioning look but nods no. "Should I?"

"Umm...No!"

He stares at me for a minute before saying. "I should head back to my room so I can get changed for Karaoke. I'm sorry if I made a fool of myself."

"It's ok!" He goes to give you a hug and you awkwardly hug him back and watch as he leaves. You stand there in shock. What the hell happened! You slowly start to get dressed from the karaoke. You laugh at the costume that Kim picked out for you but then you kinda start to feel insecure once you put it on.

You pull out your phone  
You pull out your phone.

You: Kim do I really have to wear this costume.

Kim: YES!

You sigh grabbing your bag and heading to the elevators. You get in and hit the ground floor but groan as it stops on Rob and Rich's floor. As the doors open Rob looks up from his phone seeing you and he stares making you uneasy. Then you notice his outfit and giggle.

He swallows stepping in the elevator  
He swallows stepping in the elevator. "Hey Y/N." You look away shyly just as your about to say something you hear Rich's voice from done the hall. "Damn Y/N you can be my schoolgirl any time!" Rob chuckles as I look away blushing. Rich steps in the elevator as Rob leans close to you and whispers "You okay Y/N?" You swallow "Uh...yeah" You blush more thinking about a little while ago.

He touches your arm causing a fire to burn in my core. All you can think about is the way he kissed you earlier and his words echo in your head.

I can help you not be a virgin if you want. I've got a secret Y/N! Molly and I have been separated from months now and we are filling for divorce. I haven't had sex in so long and I've always been attracted to you. You're so damn beautiful!

Your core is burning and your so lost in you're so lost in your thoughts you don't notice the elevator stop and open until you feel Rob's hand on your arm again. You look at him your eyes locking with his. "You coming Y/N?" You stare into his eyes for a moment before you look away blushing again. You slowly walk with him out the elevator and backstage where everyone else is waiting. The next hour goes extremely slow especially since all you have on your mind is having sex with Rob. Toward the end of the night. Rob, Rich, Matt, Kim and Bri are all on stage doing a song and Rob starts singing really getting into the song. You watch as his tongue darts out a few times.

He starts to play a guitar solo and as he goes to bend he looks over at you. Your eyes locking with his. The sweat rolling down his face causes your core burn again. You have to cross your legs to contain the fire within. He smirks turning his attention back to the song.

As the last song is being played you sneak away. You can't watch Rob anymore. You reach your room and close the door leaning against it. You let out a loud groan thinking.

What the hell is wrong with me! Rob is married! Even if he is separated and about to go through a divorce...He's married. Get a grip girl!

You step away from the door and start to walk to your bathroom when you hear a soft knock on your door. "Who the heck is that." You slowly walk to the door and look through the peephole and your core starts to burn instantly seeing Rob standing there.

You swallow and lean against the door. He knocks again. "Y/N?"

You calm yourself then open the door. "Yes Rob?"

"You okay? I was looking for you after the last song but Matt said you left before it ended."

You sigh and lie "Yeah I just have a little headache and music was making it worse."

"Oh okay. Can I come in?" His tongue moves across his lips causing you to grow weak.

You stare at him for a moment. "Rob i've got a headache. I really just want to turn in for the night." He stares for a moment as a smirk comes across his face. "I have the perfect cure for a headache."

You stare at him unable to say anything as you look into his eyes you notice they are a dark blue. A blue you've never noticed. "Rob please I'm tired." You go to close the door but he puts his hand out stopping you.

He walks in moving toward you. "Robbie what are you doing?"

He moves toward you his eyes burning into you. You slowly back away until you hit the wall on the other side of the room. He smirks as he moves closer and is standing inches from you again. You can feel his hot breathe and its causing you to grow hot and wet. "Rob?" He smirks again as if knowing what he's doing to you.

He puts his arms up on either side of you pinning you in as he leans in and kisses you. You stand there in shock for a moment. After a moment you grab the back of his hair and pull lightly as you begin to kiss him back. He groans into your mouth as his tongue outlines your lips. His hands wonder down to your hips. He grips them and without any effort lifts you wrapping your legs around his waist as he pins you against the wall again.

You let out a groan feeling his hardness against your core. He plunges his tongue into your mouth exploring your mouth with it. You start to panic and go to pull away. "Robbie!! Stop!! Put me down please!!"

He stops and stares at you for a moment before he puts you down but looks at you. "Y/N I'm sorry. I don't know what came over me. I've been thinking about you all day and after that game of truth or dare I've wondered what it would be like to be with you."

"Rob...I'm...a...vvviirrggann. I've never even made out with anyone." He looks back at you with a shocked look on his face. He smiles and moves close to your ear as he whispers sending chills everywhere. "So let me help you change that. We can go as slow or as fast as you want."

You stare into his now dark blue eyes for a moment. Your core is on fire and you want nothing more than to let him make love to you and make you a women but you can't shake the fact that he's still married. Separated or not he's still married. "Robbie you're still married." He smiles pulling you close to him. You groan feeling his hardness poke at your stomach. "Oh sweetheart. I may still be married but the truth is my marriage ended last year sometime. Molly and I haven't been intimate in so long I've almost forgotten what sex feels like.

He leans in to kiss you again and you let him melting into him. Before you know it your hands are undoing his pants and sliding a hand into his boxers. He lets out a groan kissing harder as his hands roam your body. "Rob!" He smirks into your neck as he starts to unbutton your shirt. He gets frustrated with the buttons so he just rips it open causing buttons to fly everywhere. He groans seeing your chest as he pushes your shirt off your shoulders. He wastes no time in getting your bra off. He kisses down your chest taking one of your breasts in his mouth causing you to let out a moan. He smirks grabbing the other as his other hand wonders to your burning core. 

You moan at pulling him closer to you. You push him away for a minute causing him to look at you. You smile and pull off his shirt pulling him back to you and kiss him hard. He pulls your skirt tossing it across the room. You let out a moan feeling his skin against yours. He grips your ass and lifts you wrapping your legs around his waist as he kisses you hard. "Robbie!" He smirks into your mouth as he walks to the bed tossing you onto it. 

He pulls his pants and boxers off and tosses them. You notice his hard erection and get slightly nervous. He notices you staring and chuckles. "I promise I'll be gentle and if any time you want to stop just tell me." You nod nervously as he climbs on top of you positioning himself between your legs. He kisses you hard for a moment before he moves to your neck where he sucks lightly sending chills all over your body. 

He kisses further down making his way down to your stomach right above your core. He pauses and starts to take off your panties tossing them. He groans taking in your bare body as he leans in liking a stripe up your slick core. You let out a loud moan at this new feeling. He smirks licking a few more times before he kisses his way back up. 

You feel his cock poking at your core and it makes you wetter and hotter. As if moving on their own your hips move upward needing him inside you. Rob smiles down at you. "You sure you're okay with this?" You moan "Robbie yes! Please!" He smirks as he reaches between the two of you and lines himself up with your core and slowly pushes in. You feel yourself stretching as he pushes in a little more. You push him off some when the pain gets to be to much. He stops looking down at you. "You okay sweetheart? We can stop." 

You smile at him "Just give me a minute to adjust." He nods waiting for you to let him continue. After a moment you push your hips up a little groaning as you feel yourself stretch more. Rob moans as he pushes in deeper. "My god your so tight!" He pushes in a little more and stops. You look up at him. He smirks "I'm all the way in sweetheart. You good?" 

You smile and move your hips groaning as the burn continues. Rob stays still for a moment allowing you to adjust to him until he can't take your slow pace anymore. "Sweetheart are you adjusted yet? This slow pace is killing me." 

You smile pulling him to you and flip so your own top. You start to bounce hard on him. He growls out "OH FUCK!" He thrusts his hips up as you come down on him going deeper. He hits your g-spot and you almost lose conrtol. Your head falls back as your head falls back. Rob smirks as he grabs your hips and starts to thrust hard. You moan loving it. He grins pulling you down to him and flips so he's on top again. He kisses you for a moment before he starts thrusting again this time hard and deep. 

You groan loving the feeling of him inside you. "Oh Rob. Don't stop!" He smirks pulling out causing you to whimper at the loss of contact. He chuckles as he stands "Come here baby I wanna try something I never could do with Molly." You crawl to him and kneel in front of him on the bed. He smiles gripping your ass and lifts you off the bed. You giggle holding onto his neck as he holds you with one arm using his other to guide himself back into your core. 

He grabs your hips again as his slowly pulls you up and down on him as he thrusts hard. You groan loving this position. "OH MY GOSH ROB!" Your head falls back as you push harder against him. He chuckles holding you close he whispers in your ear "Seems like someone is enjoying herself." You only moan as Rob bounces you on his cock. 

He pushes harder and deeper for a moment. He pulls out setting you back down. "Bend over the bed sweetheart." You smile and do as he says. Before you have time to do anything his pushing back in. You let out a groan as he grips your hips again and thrusts hard. He moves hard and fast. You groan feeling a knot in your stomach. "Robbie!" He continues moving at this pace as you push back making him go deeper. "OH MY GOSH!!! ROB!!" He groans loving moans. He pulls you up your back to his front. He kisses your neck as one of his hands reaches around and begins to rub your clit as he continues to fuck you hard. Your head falls back onto his shoulder as you feel the knot tighten. You groan out his name. 

He smiles knowing your close to release. He whispers in your ear "Let go baby! Cum for me!" You groan as he thrusts hard the knot releases and you feel yourself tighten around him. He groans out "OH FUCK!" as he feels you tighten around him and cum all over his cock. After a few more thrusts he's releasing deep inside you. His thrusts slow as you both come down from your highs. 

He stays inside you for a moment lightly kissing your neck sending chills everywhere. You shiver and he chuckles as he pulls out stepping back from you. He lays on the bed motioning for you to come lay with him. You smile and climb in next to him. You cuddle close to him. 

"Thank you Robbie!" He pulls your face up to look at you. "For what sweetheart?"

"For being gentle and caring at first. It was amazing!" 

He chuckles "Sweetheart you deserved it and so much more. I'm glad you enjoyed it especially since it was your first time." 

He kisses your forehead and pulls you close to him. You smile and think to yourself. I could get used to this. The two of you fall asleep spooning.


End file.
